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MedKoo Cat#: 341117 | Name: Brusatol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Brusatol (Brutasol) is a plant-derived natural quassinoid that exhibits broad cytotoxicity in cancer cultures (IC50 <1 μM against 457 cancer cell lines) by inhibiting de novo synthesis of cellular proteins (Effective conc. <50 nM in A549 cells), including NRF2. Brusatol has been used to study the protective role of Nrf2 (nuclear factor, erythroid 2 like 2 ) in intestinal ischemia/reperfusion induced injury.

Chemical Structure

Brusatol
Brusatol
CAS#14907-98-3

Theoretical Analysis

MedKoo Cat#: 341117

Name: Brusatol

CAS#: 14907-98-3

Chemical Formula: C26H32O11

Exact Mass: 520.1945

Molecular Weight: 520.53

Elemental Analysis: C, 59.99; H, 6.20; O, 33.81

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Brusatol; (+)-Brusatol; NSC 172924; NSC172924; NSC-172924; BRN 1444847; BRN1444847; BRN-1444847
IUPAC/Chemical Name
(11beta,12alpha,15beta)-13,20-Epoxy-3,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)-2,16-dioxopicras-3-en-21-oic acid, methyl ester
InChi Key
ZZZYHIMVKOHVIH-VILODJCFSA-N
InChi Code
InChI=1S/C26H32O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h6,12,14,17-21,29-31H,7-9H2,1-5H3/t12-,14+,17+,18+,19+,20+,21-,24-,25+,26-/m0/s1
SMILES Code
C=1([C@H]2[C@@](CC(C1O)=O)(C)[C@@H]1[C@@]34[C@@H](C2)OC([C@@H]([C@H]3[C@](C(=O)OC)(OC4)[C@H]([C@@H]1O)O)OC(\C=C(/C)C)=O)=O)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Brusatol (NSC 172924) inhibits Nrf2.
In vitro activity:
Nrf2 inhibition by Brusatol causes downregulation of the expression of glycolysis-related proteins and decreased glucose consumption and lactate production, whereas the level of ROS production was unaffected. Reference: Biomed Pharmacother. 2021 Jun 8:111652. https://pubmed.ncbi.nlm.nih.gov/34112534/
In vivo activity:
The oxygen-induced retinopathy rat model was established to mimic ROP, which was further intravitreal administrated with brusatol. Intravitreal brusatol administration could alleviate both angiogenesis and microgliosis induced by hyperoxia, along with down-regulation of vascular endothelial growth factor, vascular endothelial growth factor receptor (VEGFR)-1, VEGFR-2, cluster of differentiation molecule 11B, tumor necrosis factor alpha, inducible nitric oxide synthase, glial fibrillary acidic protein, and IBA-1 expression. It was further revealed that Nrf2 and heme oxygenease-1 were diminished by brusatol administration. The results demonstrate the potential of intravitreal brusatol deliver to treat ROP with down-regulation of angiogenesis and microgliosis. Reference: Vis Neurosci. 2021 Mar 17;38:E002. https://pubmed.ncbi.nlm.nih.gov/33729121/
Solvent mg/mL mM
Solubility
DMSO 67.0 128.71
DMSO:PBS (pH 7.2) (1:1) 0.5 0.96
DMF 1.0 1.92
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 520.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Cheng C, Yuan F, Chen XP, Zhang W, Zhao XL, Jiang ZP, Zhou HH, Zhou G, Cao S. Inhibition of Nrf2-mediated glucose metabolism by brusatol synergistically sensitizes acute myeloid leukemia to Ara-C. Biomed Pharmacother. 2021 Jun 8:111652. doi: 10.1016/j.biopha.2021.111652. Epub ahead of print. PMID: 34112534. 2. Xie J, Lai Z, Zheng X, Liao H, Xian Y, Li Q, Wu J, Ip S, Xie Y, Chen J, Su Z, Lin Z, Yang X. Apoptotic activities of brusatol in human non-small cell lung cancer cells: Involvement of ROS-mediated mitochondrial-dependent pathway and inhibition of Nrf2-mediated antioxidant response. Toxicology. 2021 Mar 15;451:152680. doi: 10.1016/j.tox.2021.152680. Epub 2021 Jan 16. PMID: 33465425. 3. Wu Z, Xu Y, Xu J, Lu J, Cai L, Li Q, Wang C, Su Z. Brusatol Inhibits Tumor Growth and Increases the Efficacy of Cabergoline against Pituitary Adenomas. Oxid Med Cell Longev. 2021 Jun 16;2021:6696015. doi: 10.1155/2021/6696015. PMID: 34221237; PMCID: PMC8221873. 4. Liang X, Wang R. The Nrf2 inhibitor brusatol has a protective role in a rat model of oxygen-induced retinopathy of prematurity. Vis Neurosci. 2021 Mar 17;38:E002. doi: 10.1017/S095252382100002X. PMID: 33729121.
In vitro protocol:
1. Cheng C, Yuan F, Chen XP, Zhang W, Zhao XL, Jiang ZP, Zhou HH, Zhou G, Cao S. Inhibition of Nrf2-mediated glucose metabolism by brusatol synergistically sensitizes acute myeloid leukemia to Ara-C. Biomed Pharmacother. 2021 Jun 8:111652. doi: 10.1016/j.biopha.2021.111652. Epub ahead of print. PMID: 34112534. 2. Xie J, Lai Z, Zheng X, Liao H, Xian Y, Li Q, Wu J, Ip S, Xie Y, Chen J, Su Z, Lin Z, Yang X. Apoptotic activities of brusatol in human non-small cell lung cancer cells: Involvement of ROS-mediated mitochondrial-dependent pathway and inhibition of Nrf2-mediated antioxidant response. Toxicology. 2021 Mar 15;451:152680. doi: 10.1016/j.tox.2021.152680. Epub 2021 Jan 16. PMID: 33465425.
In vivo protocol:
1. Wu Z, Xu Y, Xu J, Lu J, Cai L, Li Q, Wang C, Su Z. Brusatol Inhibits Tumor Growth and Increases the Efficacy of Cabergoline against Pituitary Adenomas. Oxid Med Cell Longev. 2021 Jun 16;2021:6696015. doi: 10.1155/2021/6696015. PMID: 34221237; PMCID: PMC8221873. 2. Liang X, Wang R. The Nrf2 inhibitor brusatol has a protective role in a rat model of oxygen-induced retinopathy of prematurity. Vis Neurosci. 2021 Mar 17;38:E002. doi: 10.1017/S095252382100002X. PMID: 33729121.
1: Zhang J, Fang X, Li Z, Chan HF, Lin Z, Wang Y, Chen M. Redox-sensitive micelles composed of disulfide-linked Pluronic-linoleic acid for enhanced anticancer efficiency of brusatol. Int J Nanomedicine. 2018 Feb 13;13:939-956. doi: 10.2147/IJN.S130696. eCollection 2018. PubMed PMID: 29491708; PubMed Central PMCID: PMC5815479. 2: Zhang X, Wang Y, Velkov T, Tang S, Dai C. T-2 toxin-induced toxicity in neuroblastoma-2a cells involves the generation of reactive oxygen, mitochondrial dysfunction and inhibition of Nrf2/HO-1 pathway. Food Chem Toxicol. 2018 Feb 9;114:88-97. doi: 10.1016/j.fct.2018.02.010. [Epub ahead of print] PubMed PMID: 29432840. 3: Kapur A, Beres T, Rathi K, Nayak AP, Czarnecki A, Felder M, Gillette A, Ericksen SS, Sampene E, Skala MC, Barroilhet L, Patankar MS. Oxidative stress via inhibition of the mitochondrial electron transport and Nrf-2-mediated anti-oxidative response regulate the cytotoxic activity of plumbagin. Sci Rep. 2018 Jan 18;8(1):1073. doi: 10.1038/s41598-018-19261-w. PubMed PMID: 29348410; PubMed Central PMCID: PMC5773707. 4: Chen HM, Lai ZQ, Liao HJ, Xie JH, Xian YF, Chen YL, Ip SP, Lin ZX, Su ZR. Synergistic antitumor effect of brusatol combined with cisplatin on colorectal cancer cells. Int J Mol Med. 2018 Mar;41(3):1447-1454. doi: 10.3892/ijmm.2018.3372. Epub 2018 Jan 9. PubMed PMID: 29328398; PubMed Central PMCID: PMC5819912. 5: Liu HY, Tuckett AZ, Fennell M, Garippa R, Zakrzewski JL. Repurposing of the CDK inhibitor PHA-767491 as a NRF2 inhibitor drug candidate for cancer therapy via redox modulation. Invest New Drugs. 2018 Jan 3. doi: 10.1007/s10637-017-0557-6. [Epub ahead of print] PubMed PMID: 29297149. 6: Lin Y, Sui LC, Wu RH, Ma RJ, Fu HY, Xu JJ, Qiu XH, Chen L. Nrf2 inhibition affects cell cycle progression during early mouse embryo development. J Reprod Dev. 2018 Feb 27;64(1):49-55. doi: 10.1262/jrd.2017-042. Epub 2017 Dec 16. PubMed PMID: 29249781. 7: Zhang Y, Zhang LH, Chen X, Zhang N, Li G. Piceatannol attenuates behavioral disorder and neurological deficits in aging mice via activating the Nrf2 pathway. Food Funct. 2018 Jan 24;9(1):371-378. doi: 10.1039/c7fo01511a. PubMed PMID: 29214257. 8: Wu J, Bao L, Zhang Z, Yi X. Nrf2 induces cisplatin resistance via suppressing the iron export related gene SLC40A1 in ovarian cancer cells. Oncotarget. 2017 Jul 25;8(55):93502-93515. doi: 10.18632/oncotarget.19548. eCollection 2017 Nov 7. PubMed PMID: 29212168; PubMed Central PMCID: PMC5706814. 9: Lu Z, Lai ZQ, Leung AWN, Leung PS, Li ZS, Lin ZX. Exploring brusatol as a new anti-pancreatic cancer adjuvant: biological evaluation and mechanistic studies. Oncotarget. 2017 May 10;8(49):84974-84985. doi: 10.18632/oncotarget.17761. eCollection 2017 Oct 17. PubMed PMID: 29156697; PubMed Central PMCID: PMC5689587. 10: Zhou J, Tan L, Xie J, Lai Z, Huang Y, Qu C, Luo D, Lin Z, Huang P, Su Z, Xie Y. Characterization of brusatol self-microemulsifying drug delivery system and its therapeutic effect against dextran sodium sulfate-induced ulcerative colitis in mice. Drug Deliv. 2017 Nov;24(1):1667-1679. doi: 10.1080/10717544.2017.1384521. PubMed PMID: 29078713. 11: Meng QT, Chen R, Chen C, Su K, Li W, Tang LH, Liu HM, Xue R, Sun Q, Leng Y, Hou JB, Wu Y, Xia ZY. Transcription factors Nrf2 and NF-κB contribute to inflammation and apoptosis induced by intestinal ischemia-reperfusion in mice. Int J Mol Med. 2017 Dec;40(6):1731-1740. doi: 10.3892/ijmm.2017.3170. Epub 2017 Oct 2. PubMed PMID: 29039475; PubMed Central PMCID: PMC5716448. 12: Tao S, Rojo de la Vega M, Chapman E, Ooi A, Zhang DD. The effects of NRF2 modulation on the initiation and progression of chemically and genetically induced lung cancer. Mol Carcinog. 2018 Feb;57(2):182-192. doi: 10.1002/mc.22745. Epub 2017 Nov 6. PubMed PMID: 28976703; PubMed Central PMCID: PMC5760364. 13: Oh ET, Kim CW, Kim HG, Lee JS, Park HJ. Brusatol-Mediated Inhibition of c-Myc Increases HIF-1α Degradation and Causes Cell Death in Colorectal Cancer under Hypoxia. Theranostics. 2017 Aug 11;7(14):3415-3431. doi: 10.7150/thno.20861. eCollection 2017. PubMed PMID: 28912885; PubMed Central PMCID: PMC5596433. 14: Dong F, Wang S, Wang Y, Yang X, Jiang J, Wu D, Qu X, Fan H, Yao R. Quercetin ameliorates learning and memory via the Nrf2-ARE signaling pathway in d-galactose-induced neurotoxicity in mice. Biochem Biophys Res Commun. 2017 Sep 23;491(3):636-641. doi: 10.1016/j.bbrc.2017.07.151. Epub 2017 Jul 28. PubMed PMID: 28757412. 15: Sun Q, Wu Y, Zhao F, Wang J. Maresin 1 Ameliorates Lung Ischemia/Reperfusion Injury by Suppressing Oxidative Stress via Activation of the Nrf-2-Mediated HO-1 Signaling Pathway. Oxid Med Cell Longev. 2017;2017:9634803. doi: 10.1155/2017/9634803. Epub 2017 Jul 2. PubMed PMID: 28751936; PubMed Central PMCID: PMC5511669. 16: Catanzaro E, Calcabrini C, Turrini E, Sestili P, Fimognari C. Nrf2: a potential therapeutic target for naturally occurring anticancer drugs? Expert Opin Ther Targets. 2017 Aug;21(8):781-793. doi: 10.1080/14728222.2017.1351549. Epub 2017 Jul 10. Review. PubMed PMID: 28675319. 17: Feng L, Li J, Yang L, Zhu L, Huang X, Zhang S, Luo L, Jiang Z, Jiang T, Xu W, Wang X, Jin H. Tamoxifen activates Nrf2-dependent SQSTM1 transcription to promote endometrial hyperplasia. Theranostics. 2017 Apr 10;7(7):1890-1900. doi: 10.7150/thno.19135. eCollection 2017. PubMed PMID: 28638475; PubMed Central PMCID: PMC5479276. 18: Ma R, Li H, Zhang Y, Lin Y, Qiu X, Xie M, Yao B. The toxic effects and possible mechanisms of Brusatol on mouse oocytes. PLoS One. 2017 May 18;12(5):e0177844. doi: 10.1371/journal.pone.0177844. eCollection 2017. PubMed PMID: 28542354; PubMed Central PMCID: PMC5436816. 19: Karathedath S, Rajamani BM, Musheer Aalam SM, Abraham A, Varatharajan S, Krishnamurthy P, Mathews V, Velayudhan SR, Balasubramanian P. Role of NF-E2 related factor 2 (Nrf2) on chemotherapy resistance in acute myeloid leukemia (AML) and the effect of pharmacological inhibition of Nrf2. PLoS One. 2017 May 15;12(5):e0177227. doi: 10.1371/journal.pone.0177227. eCollection 2017. PubMed PMID: 28505160; PubMed Central PMCID: PMC5432104. 20: Xiang Y, Ye W, Huang C, Lou B, Zhang J, Yu D, Huang X, Chen B, Zhou M. Brusatol inhibits growth and induces apoptosis in pancreatic cancer cells via JNK/p38 MAPK/NF-κb/Stat3/Bcl-2 signaling pathway. Biochem Biophys Res Commun. 2017 Jun 10;487(4):820-826. doi: 10.1016/j.bbrc.2017.04.133. Epub 2017 Apr 25. PubMed PMID: 28455228.

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